This invention relates to 5-amino-3-oxo-4-(substituted-phenyl)-4-pyrroline derivatives and to the use of such compounds as herbicides and plant growth regulators.
U.S. Pat. No. 3,577,433 is directed to a process for preparing a very broad genus of compounds having the formula: ##STR1## wherein R.sup.1 is a hydrocarbon group, such as alkyl, cycloalkyl, aryl, arylalkyl, alkaryl, optionally substituted with groups that are free of reactive hydrogen or (R.sup.1).sub.2 N can form a heterocycle, R is as defined for R.sup.1 or is -NR.sup.1 R.sup.1 ; and R.sup.2 and R.sup.4 are independently hydrogen, alkyl, aryl, cyclocalkyl, aralkyl, alkaryl, and the like. The compounds are described as useful as hydrogen halide acceptors and catalysts.
Tetrahedron, Vol. 25, 5721-32 (1969); CA:v 72:43329t discloses 1,4-diphenyl-3-oxo-5-dimethylaminopyrroline as part of an academic discussion. J. Organic Chemistry Vol. 41, pp. 390-2, discloses 1-ethyl-2-(2-carboxyphenyl)-3-oxo-4-phenyl-pyrroline in an academic paper. Based on Chem. Abstracts Vol. 92:41753r, Russian patent document SU No. 687070 discloses 1,4-diphenyl-3-oxo-5-aminopyrroline and the corresponding 2-methyl, ethyl and phenyl derivatives thereof and Chem. Abstracts Vol. 89:163331 describes a paper by Dopov. of the Akad. Nauk. Ukr. RSR, in Ser. B. Geol., Khim. Biol Nauk, Vol. (7), pp. 619-21 as disclosing 1,4-diphenyl-2,2-dimethyl-3-oxo-4-aminopyrroline. Japanese patent document No. 69/5222 (1969)--Chem. Abstracts Vol. 70:115004S discloses 1-methyl-3-oxo-4-phenyl-5-aminopyrroline as a pharmaceutical.
Chemiker-Zeitung 104 (1980) No. 10, Pages 302-303, is an academic paper disclosing the ring closure of 1-(dimethylamino)-2,4-diphenyl-1-buten-3,4-dione to yield 5-dimethylamino-2,4-diphenyl-2,3-dihydrofuran. British Pat. No. 1,521,092, discloses certain 3-phenyl-5-substituted-4(1H)-pyrid-ones or -thiones as herbicides. Japanese Patent Application No. 13,710/69 (Chemical Abstracts 71:61195e) discloses 5-amino-3-oxo-4-(phenyl or 4-chlorophenyl)-2,3-dihydrofurans. Japanese Pat. No. 19090 (Chemical Abstracts 69P10352e) discloses certain 2,3-dihydrothiophenes as pharmaceuticals. Helvetica Chemica Acta, Volume 66, Pages 362-378 (1983) discloses 5-N-cyclopropyl-4-phenyl-2-methoxycarbonylmethylene-3-furanone as part of an academic chemical synthesis discussion.
In my prior application, Ser. Nos. 505,169; 594,497; and 607,610 filed June 17, 1983, now abandoned; Mar. 29, 1984, now U.S. Pat. No. 4,537,673; and May 9, 1984; now abandoned, respectively, I disclosed certain herbicidally active derivatives of 5-amino-3-oxo-4-substituted phenyl-2,3-dihydrofuran. In my application Ser. No. 623,805, filed June 23, 1984, now U.S. Pat. No. 596,595, I disclosed certain herbicidally active 5-amino-3-oxo-4-substituted phenyl2,3-dihydrothiophene derivatives.